SMB00609

6,6′-Dihydroxythiobinupharidine

≥95% (HPLC)

• Sinonimo/i: 6,6′-Dihydroxythionuphlutine A, Nuphleine
• Formula empirica (notazione di Hill): C₃₀H₄₂N₂O₄S
• Numero CAS: 30343-70-5
• Peso molecolare: 526.73
• Codice UNSPSC: 51102829
• NACRES: NA.76

Proprietà

• Livello qualitativo: 200
• Saggio: ≥95% (HPLC)
• Stato: powder
• Spettro attività antibiotica: Gram-positive bacteria
• Modalità d’azione: enzyme | inhibits
• Temperatura di conservazione: −20°C
• Stringa SMILE: O[C@H]1N2[C@@]([C@H](C)CC[C@H]2C3=COC=C3)([H])CC[C@@]14SC[C@]5(C4)CC[C@]([C@H](C)CC[C@H]6C7=COC=C7)([H])N6[C@@H]5O
• InChI: 1S/C30H42N2O4S/c1-19-3-5-25(21-9-13-35-15-21)31-23(19)7-11-29(27(31)33)17-30(37-18-29)12-8-24-20(2)4-6-26(32(24)28(30)34)22-10-14-36-16-22/h9-10,13-16,19-20,23-28,33-34H,3-8,11-12,17-18H2,1-2H3/t19-,20-,23+,24+,25+,26+,27-,28-,29-,30+/m1/s1; DYEOLAMWQVWASS-XKCSGWQSSA-N

Descrizione

Descrizione generale

6,6′-Dihydroxythiobinupharidine is an active compound found in Nuphar lutea extract. It is a dimeric sesquiterpene thioalkaloid which presents multiple activities.[1]

Azioni biochim/fisiol

6,6′-Dihydroxythiobinupharidine inhibits NFκB activation, leading to an induction of apoptosis via cleavage of procaspase-9 and poly (ADP-ribose) polymerase (PARP).

It was also found to act synergistically with cytotoxic drugs such as cisplatin and etoposide, enabling their cytotoxic effect at lower concentrations.[2]

6,6′-Dihydroxythiobinupharidine was found to have cytotoxic activity at a concentration of ~10 μM on human leukemia cells (U937), mouse melanoma cells (B16F10), and human fibroblasts (HT1080).[3]

In addition, Nuphar lutea extract was effective against both Leishmania promastigote and amastigote forms (IC₅₀ = 2 ± 0.12 μg/mL; ID₅₀ = 0.65 ± 0.023 μg/mL; LD₅₀ = 2.1 ± 0.096 μg/mL, STI = 3.23). A synergistic antileishmanial activity was demonstrated with the antileishmanial drug, paromomycin.[4]

Recently 6,6′-dihydroxythiobinupharidine was found to be active against MRSA and VRE strains with an MIC of 1-4 μg/mL. Inhibition of DNA topoisomerase IV but not DNA gyrase in S. aureus was suggested as the mechanism of action.[5] 6,6′-Dihydroxythiobinupharidine was also shown to promote neutrophil effector bactericidal functions.[6]

Informazioni sulla sicurezza

• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable